Dimethyl Sulfoxide → 4-(5-Chloro-2-pyrimidinyl)-3-nitroaniline

HRID 653410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653410
Cl[C:2]1[N:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.CS(C)=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17](O)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:8][C:5]1[CH:4]=[N:3][C:2]([C:17]2[CH:18]=[CH:19][C:14]([NH2:13])=[CH:15][C:16]=2[N+:21]([O-:23])=[O:22])=[N:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 5906412,5-DichloropyrimidineHCID 34174194-Amino-2-Nitrophenol

Produkt 1

HCID 201946804-(5-Chloro-2-pyrimidinyl)-3-nitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

1.43 g of 2,5-dichloropyrimidine was dissolved in 20 mol of dimethyl sulfoxide. To this solution, a mixture of 1.50 g of 4-amino-2-nitrophenol and 5 ml of water, and 2.69 g of potassium carbonate were added, and the mixture was reacted in the atmosphere of nitrogen gas at a temperature of from 100° to 110° C. for 2 hours. After the completion of the reaction, the reaction product was poured into water, and extracted with methylene chloride. The extract layer was washed with brine and dried over anhydrous sodium sulfate, and purified by silica gel column chromatography, whereby 0.74 g of 4-(5-chloro-2-pyrimidinyl)-3-nitroaniline having a melting point of from 151° to 152° C., was obtained.

Aufarbeitung

  1. additionwere added
  2. customthe mixture was reacted in the atmosphere of nitrogen gas at a temperature of from 100° to 110° C. for 2 hours
  3. customAfter the completion of the reaction
  4. extractionextracted with methylene chloride
  5. washThe extract layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. custompurified by silica gel column chromatography, whereby 0.74 g of 4-(5-chloro-2-pyrimidinyl)-3-nitroaniline having a melting point of from 151° to 152° C.
  8. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-d7d16c1e695c4613b2736ebd0cc7678f
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04677111

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